Pretty Dean
by Miss Elucidation
Summary: Dean hates that stupid "hooker with a heart of gold" trope, and Gabriel really wants Castiel to get laid. AU


**AN: Oh my gosh I can't believe I wrote this... **

**There was a picture prompt on tumblr from the Den of Iniquity scene of Cas looking terrified and Dean holding a wad of bills with the caption:**

**"**Cas just looks so scared it's adorable.

can we turn it into a hooker!au, please? cas just came out to his older brother, gabriel (which was as subtle as standing on the top of a roof, screaming _i'm gay_ at people below), and said brother is all, 'i knew it! now get dressed, we gotta get you laid, baby bro.'

cas is ready to bite and scratch, but he's also a bit curious because he's one of those people who figure out their preference around their mid-life crisis, and let's get real, porn and masturbation doesn't even come close to the real deal. so they end up at a strip club, and it turns out it's one of gabe's favourite places, and he knows who to look for.

and later, after flipping through the wad of cash gabriel gave him, dean looks at cas, raises his eyebrows, and says, 'for _that_, i can teach you all i know, and then some.' **"**

**It's uh... not exactly the prompt but... excuse me while I go drown myself. **

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><p>Dean had never liked the "hooker with a heart of gold" trope, and not just because he liked his ladies quick and easy without a soppy backstory. No, what pissed Dean off was that he knew what it was like to be broke as shit, and thus there were ways to survive without having to sell one's body. One particularly bad year, when Sammy was just a freshman in High School, he had worked three jobs. So, this whole "oooh, I have no alternative" shit was just that. Shit. If you were in a jam, all you needed to do was dig your heels in, and work your ass out of it.<p>

At least, that was how Dean had felt until Sam dicked off to Lawyer Academy. That's not to say the older Winchester resented his brother, in fact he was actually exceptionally proud of the kid's intelligence and achievements. But damn if that tuition bill didn't fuck him every month.

Uh… literally.

"Dean? Dean!"

Pamela's cuff upside his head brought him out of his musings.

"Ah! Whaddya want, you shrew?" Dean moaned pathetically.

A familiar, smarmy grin grew on the woman's face. "You're up, Big Boy." She nodded over to a table in the corner before picking up a tray of empty glasses and moving to the back of the bar.

And 'lo, Dean suddenly worked night shifts at a joint called _The Roadhouse_ in order to _pay his way through college_. He was the quintessential Hooker with a fucking Heart of Gold. Cursing God, Jesus, and Julia Roberts, Dean performed his nightly mental ritual of shedding his self-respect, pressing it gently and placing it on a hanger for safe keeping before making his way to the two men at the table in the corner.

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><p>"We shouldn't be here."<p>

Gabriel choked on his drink, laughing at Castiel's frozen expression of horror.

"Of course we should, Cassy-babe, we gon' get you laid!" the trickster quipped gleefully. "YO, WAITRESS! I'd like an appletini mixed with three shots of Cupcake Vodka—oh, and some tequila for the little tike over there, thanks darling!" Gabe smiled in utter enjoyment at the woman.

"No! Not—not… tequila…" Castiel squeaked pathetically at the lady's retreating back. "Gabriel you know what happened the last time—"

Gabe tucked the bar napkin into his shirt like a cravat before digging into his cheese fries. "Of course I do, little bro. I'm doing you a favor."

He should have known not to tell Gabriel about his sexuality. Up until last week when the wide-eyed man had revealed to his brother his preference for… not-women… Gabriel had simply assumed that he was asexual. And now that he knew… well. Gabe hadn't left him alone until he agreed to go out. In fact, it took most of the younger man's energy to convince his brother not to wear his signature stick-on moustache to the joint. Castiel was banging his head onto the table when the ah… worker finally showed up.

"Hey."

The man's voice was deep and friendly, and ohgoshhedoesn'

"Hey, man. This is my brother, Castiel." Gabriel replied jovially.

And now Castiel needed to be polite. So he forced his head off the table, making eye contact with the worker for a split second before looking back at the table. "H-Hello." He tried to force his face into something less pinched but found that he couldn't.

The worker scratched the back of his neck, lips quirked in silent amusement at Castiel's terror. "Uh… you guys need more time or something?"

Gabriel hopped out of his seat and bodily yanked Castiel up, surprisingly strong for such a small frame. "Nah, he's good." Reaching into his pocket, Gabe handed Castiel a wad of bills. "Here. This'll cover it. There's enough in here for the whips and chains I know you'll want, because secretly, Castiel? You're probably one kinky bastard." The trickster laughed and clapped his brother on the back before pushing him towards the man.

Castiel looked slightly green as he handed the roll of cash to the worker, startled blue eyes never moving from the man's clavicle.

"Thanks, man." The worked huffed in barely suppressed amusement.

They two were almost to the backroom when Gabriel called out to them. They turned in tandem as the shorter man caught up to them, cheeky grin in place. "Forgot to give you this." He said as he stuffed something into Castiel's hands.

They were the most obscene handcuffs ever conceived. They were fuzzy. And Pink. And had sparkles. And had the words, "like a virgin" printed in cursive across both cuffs. Castiel nearly dropped them, his face burning.

The blonde worker raised an eyebrow before smirking and taking the toy from his charge. "Alright, Rihanna, let's do this thing." He began moving down the hall again.

When Castiel turned pleading eyes to Gabriel, the man simply waved with two fingers before disappearing again.

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><p>Castiel sat on the bed in the middle of the room like it was going to rise up and eat him at any moment.<p>

After closing the door carefully, Dean sat next to the man, a careful distance away."I'm ah… I'm Dean." He tugged at a loose thread on the bed.

"Hello, Dean."

Castiel was finally looking at him now. Unblinkingly. With an expression like Dean had eaten his children alive in front of him. Christ, he wasn't that scary.

"I'm gonna go out on a limb here and guess that you don't want to do this." Dean hazarded sarcastically.

The blue-eyed man shook his head frantically.

"…Okay." Flopping backwards onto the bed, Dean stared up at the mirror on the ceiling. For several long, uncomfortable minutes, the two said nothing. Until finally he couldn't stand it anymore. "So what—You're Holden and I'm Sunny?"

Castiel's shoulders drooped. "That depends. Are you a phony?"

Lifting his head up slightly in surprise, Dean thought he saw the other man quirk a small smile. "I'm only workin' this gig so I can raise enough money to go to New York and start my career."

"Oh yes?" Castiel inquired politely.

"Yeah! As a table-dancer." Dean grinned widely when he got a smile out of the other.

And like that, A Hooker with a Heart of Gold spent the rest of the night trying to make a Blushing Virgin laugh.


End file.
